Madonna Dated Tupac, But He's Not The Only Surprising Celeb Her Madgesty Had A Relationship With

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Oh, Madonna. What are we gonna do with you? Even though the 56-year-old Rebel Heart singer has been in the blinding bright spotlight ever since her career began more than three decades ago, she’s still managed to keep some secrets close to her chest. On Howard Stern on Wednesday, the shock-jock asked her why she was ornery in an interview with David Letterman in 1994, and Madonna said she was feeling “gangsta” at the time. Why? Because Madonna was dating Tupac Shakur. WTF?!Although at first it’s tough to imagine Madonna dating the iconic West Coast rapper, she’s had a long, strange dating history as varied as her career itself. Some of her more well-known paramours include Sean Penn and her longtime husband, director Guy Ritchie who she was married to from 2000 to 2008. But she's had some lesser known and even more interesting relationships and affairs. Here are some of Madonna’s most bizarre trysts that you might not know about.

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